We present an exploratory study of an everyday navigation planning situation, addressing spatial planning strategies as well as cognitive shifts between the visually available map and the conceptualized real-world environment. Participants were asked to plan a diversified holiday route on an island, with the help of a map representing spatial as well as activity information. Following the task proper, they reported in written form about the problem-solving process. Route trajectories were analyzed with respect to their properties, and reports were analyzed with respect to the represented concepts and linguistic patterns. Results reveal that route trajectories tended to be circular rather than random, with relatively few detours or crossing lines. The underlying spatial planning strategies as represented in the written reports resembled earlier findings on the Traveling Salesperson Problem, providing insights into the extent to which this abstract task transfers to a naturalistic scenario. Most crucially, our linguistic analysis provides new results about the representation of conceptual layers when considering the real-world navigation domain of traveling in relation to the actual table-top map planning domain.